Nitrogen → 7-Chloroquinoline

Participants

Reaction Steps

4,7 Dichloroquinoline (10 g, 50 mmol) in THF (100 ml) was degassed with N2 for 5 min. PdCl2dppf (1.2 g, 2 mmol), TMEDA (9.97 g, 86 mmol), and NaBH4 (3.24 g, 86 mmol) were added and the mixture was stirred at room temperature for 5 h. Brine (20 ml) was added dropwise and the solvent was removed in vacuo. The residue dissolved in EtOAc (200 ml), dried (MgSO4) and concentrated in vacuo. The crude residue was purified by column chromatography with heptane/EtOAC (4:1-1:1 gradient) as the eluent to give the title compound (5.4 g, 65%).

Provenance & Evidence